反応式
[C:1]1([NH:7][C:8]2[C:13]([C:14](=[O:16])[CH3:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19](=[O:29])[C:20]1[CH:25]=[CH:24][C:23]([CH:26]=O)=[C:22]([F:28])[CH:21]=1.C[O-].[Na+].Cl>CO.O>[CH3:17][O:18][C:19](=[O:29])[C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:15]/[C:14](=[O:16])[C:13]2[C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:22]([F:28])[CH:21]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 25 °C
実験手順
A mixture of 1-(2-phenylamino-pyridin-3-yl)-ethanone (700 mg, 3.3 mmol) in methanol (16.5 mL) at 25° C. was treated with 3-fluoro-4-formyl-benzoic acid methyl ester (601 mg, 3.3 mmol, calculated from 50% mixture) and sodium methoxide in methanol (4.37M, 1.51 mL, 6.6 mmol). The reaction was stirred at 25° C. for 48 h. At this time, the reaction was diluted with water (50 mL), neutralized with a 2N aqueous hydrochloric acid solution, and extracted with methylene chloride (3×75 mL). The combined organics were dried over sodium sulfate and filtered. Silica gel was added to the filtrate, concentrated in vacuo and dried under high vacuum. Flash Chromatography (40 g silica column, 1% methanol/methylene chloride) afforded 3-fluoro-4-[(E)-3-oxo-3-(2-phenylamino-pyridin-3-yl)-propenyl]-benzoic acid methyl ester (1 g, 80.6%) as a red solid.
後処理
- extractionextracted with methylene chloride (3×75 mL)
- dry with materialThe combined organics were dried over sodium sulfate
- filtrationfiltered
- additionSilica gel was added to the filtrate
- concentrationconcentrated in vacuo
- customdried under high vacuum
出典と根拠
- ORDレコード
- ord-54199c83a21a40feab8c1485e87a81d6
- 出典データセット
- uspto-grants-2013_06
- 特許番号
- US08471027B2
関連ノート
読み込み中…